1,2-Dichloroethane → N-Methyl-N-[(1-methyl-1H-indol-2-yl)methyl]-2-phenoxybenzamide

HRID 1581687ノート

反応式

HRID 1581687 の反応式
C(Cl)CCl.[O:5]([C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:21][N:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[C:23]1[CH2:31][NH:32][CH3:33].C1C=CC2N(O)N=NC=2C=1.O.C(N(CC)CC)C>CN(C=O)C>[CH3:33][N:32]([CH2:31][C:23]1[N:22]([CH3:21])[C:30]2[C:25]([CH:24]=1)=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:14](=[O:16])[C:13]1[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=1[O:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

参加物

8

反応物 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 752372-Phenoxybenzoic acidHCID 757711-HydroxybenzotriazoleHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amine

生成物 1

HCID 9799521N-Methyl-N-[(1-methyl-1H-indol-2-yl)methyl]-2-phenoxybenzamide収率 106.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

EDC (230 mg, 1.2 mmole) was added to a solution of 2-phenoxybenzoic acid (214.2 mg, 1.0 mmole), 1-methyl-2-(methylaminomethyl)indole (209.1 mg, 1.2 mmole), HOBt.H2O (162.2 mg, 1.2 mmole), and triethylamine (0.35 mL, 2.5 mmole) in DMF (5 mL) at RT. After 16.5 hr, the reaction was concentrated, and the residue was reconcentrated from xylenes/CHCl3 to remove residual DMF. Flash chromatography on silica gel (40% EtOAc/hexanes) gave the title compound (393.5 mg, quantitative) as a nearly colorless, very viscous oil: 1H NMR (360 MHz, CDCl3) indicated an approximately 5:1 mixture of amide rotamers; for the major rotamer: δ 7.56 (d, J=7.9 Hz, 1H), 6.98-7.50 (m, 9H), 6.95 (d, J=7.6 Hz, 2H), 6.87 (d, J=7.5 Hz, 1H), 6.49 (s, 1H), 4.40-5.40 (m, 2H), 3.62 (s, 3H), 2.84 (s, 3H); for the minor rotamer: δ 6.80-7.50 (m, 13H), 6.47 (s, 1H), 4.40-5.40 (m, 2H), 3.56 (s, 3H), 2.98 (s, 3H); MS (ES) m/e 371 (M+H)+.

後処理

  1. customat RT
  2. concentrationthe reaction was concentrated
  3. customto remove residual DMF

出典と根拠

ORDレコード
ord-084de7fd291744b6b9cf0236632b5952
出典データセット
uspto-grants-2004_05
特許番号
US06730684B1

反応ノート

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