Potassium Phosphate, Tribasic → 2-(8-tert-Butyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde

HRID 1879674ノート

反応式

HRID 1879674 の反応式
Br[C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N:10]2[C:16](=[O:17])[C:15]3[CH:18]=[CH:19][C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:21][C:14]=3[NH:13][CH2:12][CH2:11]2)[C:3]=1[CH:4]=[O:5].[CH3:26][N:27]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[C:29]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([C:49]([N:51]3[CH2:56][CH2:55][O:54][CH2:53][CH2:52]3)=[O:50])=[CH:45][N:44]=2)[C:28]1=[O:57].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(O)CCC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:22]([C:20]1[CH:19]=[CH:18][C:15]2[C:16](=[O:17])[N:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:2]([C:31]4[CH:30]=[C:29]([NH:42][C:43]5[CH:48]=[CH:47][C:46]([C:49]([N:51]6[CH2:56][CH2:55][O:54][CH2:53][CH2:52]6)=[O:50])=[CH:45][N:44]=5)[C:28](=[O:57])[N:27]([CH3:26])[CH:32]=4)[C:3]=3[CH:4]=[O:5])[CH2:11][CH2:12][NH:13][C:14]=2[CH:21]=1)([CH3:24])([CH3:23])[CH3:25]

参加物

7

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 592164661-Methyl-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-oneHCID 595485362-Bromo-6-(8-tert-butyl-5-oxo-1,2,3,5-tetrahydrobenzo[e][1,4]diazepin-4-yl)-benzaldehyde

生成物 1

HCID 595485292-(8-tert-Butyl-5-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-6-{1-methyl-5-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-6-oxo-1,6-dihydro-pyridin-3-yl}-benzaldehyde

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 2631-Butanol溶媒

反応条件

温度
100 °C

実験手順

2-Bromo-6-(8-tert-butyl-5-oxo-1,2,3,5-tetrahydrobenzo[e][1,4]diazepin-4-yl)-benzaldehyde (0.100 g, 0.23 mmol),1-Methyl-3-[5-(morpholine-4-carbonyl)-pyridin-2-ylamino]-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyridin-2-one (0.091 g, 1.0 eq), xantphos (12 mg, 0.09 eq), and potassium phosphate (0.096 g, 2 eq) were taken up in n-butanol (3 mL) and water (0.5 mL) and a stream of argon was bubbled through the mixture for 1 minute. Pd(dba)2 (0.008 g, 0.06 eq) was added and argon was bubbled through for an additional minute. The reaction was heated under argon and stirred at 100° C. for 3 hours. The reaction was cooled, solvent was removed under vacuum, and placed directly on a silica gel column, eluted with 100% ethyl acetate, then 4% MeOH in CH2Cl2 to give the title compound as a brown solid, 76 mg as a 60:40 mixture (the title compound as the major component) with an impurity and used without further purification.

後処理

  1. customwater (0.5 mL) and a stream of argon was bubbled through the mixture for 1 minute
  2. customargon was bubbled through for an additional minute
  3. temperatureThe reaction was heated under argon
  4. temperatureThe reaction was cooled
  5. customsolvent was removed under vacuum
  6. washeluted with 100% ethyl acetate

出典と根拠

ORDレコード
ord-60c9bd9eaa1f465dbf24f0519fe61950
出典データセット
uspto-grants-2012_11
特許番号
US08318719B2

反応ノート

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