Potassium Carbonate → (R)-1-(2-Hydroxy-1-phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 388090

反応式

HRID 388090 の反応式
[NH2:1][C:2]1[C:3]([NH:18][C@H:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][OH:21])=[N:4][C:5]([C:8]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:9]=2[CH:10]=[CH:11][CH:12]=[N:13]3)=[CH:6][N:7]=1.NC1C(N[C@H](C2C=CC=CC=2)[CH2:38][OH:39])=NC(Br)=CN=1.N1C2C=CC=C(B(O)O)C=2C=CC=1.C(=O)([O-])[O-].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)C=O.O>[OH:21][CH2:20][C@H:19]([N:18]1[C:3]2=[N:4][C:5]([C:8]3[CH:17]=[CH:16][CH:15]=[C:14]4[C:9]=3[CH:10]=[CH:11][CH:12]=[N:13]4)=[CH:6][N:7]=[C:2]2[NH:1][C:38]1=[O:39])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 5153389Quinolin-5-ylboronic acidHCID 66699883(R)-2-(3-Amino-6-(quinolin-5-yl)pyrazin-2-ylamino)-2-phenylethanolHCID 86626383(R)-2-(3-Amino-6-bromopyrazin-2-ylamino)-2-phenylethanol

生成物 1

HCID 66699661(R)-1-(2-Hydroxy-1-phenylethyl)-6-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one収率 67%

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

(R)-2-(3-Amino-6-(quinolin-5-yl)pyrazin-2-ylamino)-2-phenylethanol. (R)-2-(3-Amino-6-bromopyrazin-2-ylamino)-2-phenylethanol (0.700 g, 2.26 mmol), quinoline-5-boronic acid (0.431 g, 2.48 mmol), tetrakis(triphenylphosphine)-palladium (0.287 g, 0.226 mmol), potassium carbonate (1.24 g, 9.04 mmol), water (8 mL) and dimethylformamide (35 mL) were reacted according to General Procedure B. The crude material was purified via Biotage silica gel chromatography (40-100% ethyl acetate/hexanes, 40S column) to afford the title compound (0.546 g, 67% yield). MS (ESI) m/z 358.3 [M+1]+.

後処理

  1. customThe crude material was purified via Biotage silica gel chromatography (40-100% ethyl acetate/hexanes, 40S column)

出典と根拠

ORDレコード
ord-6b82a80abef44d32a1dbd67b80dfdd53
出典データセット
uspto-grants-2013_02
特許番号
US08372976B2

関連ノート

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