1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 24961821、化合物

HRID 1662853ノート

反応式

HRID 1662853 の反応式
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[CH2:26]([NH:33][S:34]([C:37]1[CH:42]=[CH:41][C:40]([CH3:43])=[C:39](Br)[CH:38]=1)(=[O:36])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.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.CC(C)([O-])C.[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:26]([NH:33][S:34]([C:37]1[CH:38]=[CH:39][C:40]([CH3:43])=[C:41]([NH:1][C:2]2[CH:7]=[N:6][C:5]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([S:15](=[O:17])(=[O:16])[NH:18][CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:11][CH:10]=3)=[N:4][CH:3]=2)[CH:42]=1)(=[O:36])=[O:35])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

7

反応物 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 7213295N-benzyl-3-bromo-4-methylbenzenesulfonamideHCID 23665647Potassium tert-butoxideHCID 58748706HCID 58748706、化合物

生成物 1

HCID 24961821HCID 24961821、化合物収率 58%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

実験手順

A suspension of intermediate 45 (Example 93) (0.10 g, 0.28 mmol), N-benzyl-3-bromo-4-methyl-benzenesulfonamide (0.10 g, 0.29 mmol), Pd(OAc)2 (5 mg, 0.022 mmol), Xantphos (26 mg, 0.045 mmol) and potassium tert-butoxide (70 mg, 0.63 mmol) in a mixture of dioxane/DNIF (2/1, 3 mL) was sealed in a microwave reaction tube and irradiated with microwave at 150° C. for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (10% MeOH/DCM to 25% MeOH and 2% TEA/DCM) to afford the title compound (0.10 g, 58%) as a white solid.

後処理

  1. customwas sealed in a microwave reaction tube
  2. customirradiated with microwave at 150° C. for 20 min
  3. customthe cap was removed
  4. filtrationthe resulting mixture filtered
  5. washthe filtered solid washed with DCM
  6. concentrationThe filtrate was concentrated
  7. customthe residue purified by flash chromatography on silica gel (10% MeOH/DCM to 25% MeOH and 2% TEA/DCM)

出典と根拠

ORDレコード
ord-df72e65fef484d8db79887f1aec82288
出典データセット
uspto-grants-2011_10
特許番号
US08030487B2

反応ノート

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