Diisopropylethylamine → 2-chloro-4-[(1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester

HRID 2235076

反応式

HRID 2235076 の反応式
F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(C(C)C)CC)(C)C.[NH:34]1[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([C:43]([OH:45])=O)[CH:41]=2)[CH:36]=[CH:35]1.[CH3:46][O:47][C:48](=[O:57])[C:49]1[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][C:50]=1[Cl:56]>O1CCCC1>[CH3:46][O:47][C:48](=[O:57])[C:49]1[CH:54]=[CH:53][C:52]([NH:55][C:43]([C:40]2[CH:41]=[C:42]3[C:37]([CH:36]=[CH:35][NH:34]3)=[CH:38][CH:39]=2)=[O:45])=[CH:51][C:50]=1[Cl:56]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 5952301H-indole-6-carboxylic acidHCID 2733179PyBroPHCID 11839197Methyl 4-Amino-2-chlorobenzoate

生成物 1

HCID 686973742-chloro-4-[(1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester収率 26%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (8.3 g, 17.8 mmol, 1.1 equiv.) and diisopropyl ethyl amine (4.4 ml, 33.9 mmol, 2.1 equiv.) were added to 1H-indole-6-carboxylic acid (2.6 g, 16.2 mmol, 1 equiv.) in tetrahydrofuran (30 mL) and the mixture was shaken for 5 minutes at room temperature. 4-Amino-2-chlorobenzoic acid methyl ester (3.3 g, 17.9 mmol, 1.1 equiv.) was added and the resultant mixture was shaken at room temperature for 16 hours. The solvent was removed under vacuum and the residue triturated with dichloromethane (10 mL). The solid was filtered to afford 2-chloro-4-[(1H-indole-6-carbonyl)-amino]-benzoic acid methyl ester, 1.4 g (26% yield). LC @215 nm; Rt 1.36: 90%, m/z (ES+): 329 (M+H+.); δH (400 MHz; d6-DMSO) 11.65 (1H, s), 10.59 (1H, s), 8.16 (1H, s), 8.10 (1H, s), 7.93 (2H, m), 7.65 (2H, s), 7.59 (1H, m), 6.62 (1H, s), 3.85 (3H, s).

後処理

  1. customThe solvent was removed under vacuum
  2. customthe residue triturated with dichloromethane (10 mL)
  3. filtrationThe solid was filtered

出典と根拠

ORDレコード
ord-f6120e17224a4b6085e2cad556988c9b
出典データセット
uspto-grants-2010_05
特許番号
US07713996B2

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