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

HRID 2235076

반응식

HRID 2235076 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f6120e17224a4b6085e2cad556988c9b
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07713996B2

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