Potassium Phosphate, Tribasic → US8975415, RP53b

HRID 594905노트

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HRID 594905 반응식
Br[C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[O:16][CH2:15][C:11]1([CH2:14][O:13][CH2:12]1)[C:5]12[CH2:9][O:8][C:7]([NH2:10])=[N:6]1.[C:20]([C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[N:27][CH:28]=1)#[C:21][CH3:22].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.C1(/C=C/C(=O)/C=C/C2C=CC=CC=2)C=CC=CC=1.[Pd]>[C:20]([C:23]1[CH:24]=[C:25]([C:2]2[CH:3]=[C:4]3[C:17](=[CH:18][CH:19]=2)[O:16][CH2:15][C:11]2([CH2:14][O:13][CH2:12]2)[C:5]23[CH2:9][O:8][C:7]([NH2:10])=[N:6]2)[CH:26]=[N:27][CH:28]=1)#[C:21][CH3:22]

참가 물질

7

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 574164825-(1-Propynyl)pyridine-3-boronic Acid (contains varying amounts of Anhydride)HCID 867243126'-Bromodispiro[1,3-oxazole-4,4'-chromene-3',3''-oxetan]-2-amine

생성물 1

HCID 86724311US8975415, RP53b수율 42.9%

시약·촉매·용매 2

HCID 15673654(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one palladium촉매HCID 6228Dimethylformamide용매

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온도
110 °C

실험 절차

The mixture of 6′-bromodispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-amine (650 mg, 2.00 mmol), [5-(prop-1-yn-1-yl)pyridin-3-yl]boronic acid (644 mg, 4.00 mmol), (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one-palladium (3:2) (92 mg, 0.10 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (164 mg, 0.400 mmol), and K3PO4 (1.70 g, 8.00 mmol) in DMF (13 mL) was stirred for 16 hours at 110° C. under argon atmosphere. The precipitate formed was removed by filtration with celite and washed with CHCl3. The filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (CHCl3:MeOH=99:1-95:5) to give 6′-[5-(prop-1-yn-1-yl)pyridin-3-yl]dispiro[1,3-oxazole-4,4′-chromene-3′,3″-oxetan]-2-amine (310 mg).

후처리

  1. customThe precipitate formed
  2. customwas removed by filtration with celite
  3. washwashed with CHCl3
  4. concentrationThe filtrate was concentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (CHCl3:MeOH=99:1-95:5)

출처 및 근거

ORD 기록
ord-a8358e7f9fdd49e48cd37310ced664ad
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242973B2

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