4-Carboxy-3-fluorobenzeneboronic acid pinacol ester → 2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone

HRID 646410ノート

反応式

HRID 646410 の反応式
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][NH:9]1.[F:13][C:14]1[CH:22]=[C:21]([B:23]2[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]2)[CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17]>>[F:13][C:14]1[CH:22]=[C:21]([B:23]2[O:27][C:26]([CH3:28])([CH3:29])[C:25]([CH3:31])([CH3:30])[O:24]2)[CH:20]=[CH:19][C:15]=1[C:16]([N:9]1[CH2:10][CH2:11][CH2:12][C@H:8]1[CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C@H:2]1[CH3:1])=[O:17]

参加物

3

反応物 2

HCID 447176654-Carboxy-3-fluorobenzeneboronic acid pinacol esterHCID 46911921(R)-2-methyl-1-((S)-pyrrolidin-2-ylmethyl)pyrrolidine

生成物 1

HCID 579800402-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl[2-(S)-(2-(R)-methyl-pyrrolidin-1-ylmethyl)-pyrrolidin-1-yl]-methanone

実験手順

A 100 mL toluene/EtOH mixture of commercially available 4-carboxy-3-phenyl boronic acid and pinacol is stirred at 75-80° C. for 2 hours, then concentrated, slurried in toluene, concentrated, and dried in vacuo to give 2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid that is used without further purification. The title intermediate is prepared in a manner substantially analogous. General Procedure E using 2-(R)-methyl-1-(2-(S)-pyrrolidinylmethyl)pyrrolidine and 2-Fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid. The crude product is confirmed by NMR and MS (MS+) 417.5 (M+H)+ then used without further purification.

後処理

  1. customis used without further purification
  2. custom(M+H)+ then used without further purification

出典と根拠

ORDレコード
ord-6d95e6db6f9a421a811677d821323c94
出典データセット
uspto-grants-2010_04
特許番号
US07705025B2

反応ノート

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