Diisopropylethylamine → HCID 59451431, compound

HRID 1875015Notes

Reaction equation

HRID 1875015 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[C:17]([Cl:19])[CH:18]=2)[C:14]#[N:15])[C:6]([Cl:9])=[CH:7][CH:8]=1.[Cl:21][C:22]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]2[C:23]=1[CH:24]=[C:25]([C:32](Cl)=[O:33])[NH:26]2.C(N(C(C)C)CC)(C)C>ClCCl.O>[Cl:21][C:22]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]2[C:23]=1[CH:24]=[C:25]([C:32]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[C:5]([O:10][C:11]3[CH:12]=[C:13]([C:14]#[N:15])[CH:16]=[C:17]([Cl:19])[CH:18]=3)[C:4]=1[F:20])=[O:33])[NH:26]2

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 28007564,6-dichloro-1H-indole-2-carbonyl chlorideHCID 594513923-{[3-(Aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile

Product 1

HCID 59451431HCID 59451431, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-{[3-(aminomethyl)-6-chloro-2-fluorophenyl]oxy}-5-chlorobenzonitrile (0.050 g, 0.16 mmol) in dichloromethane (1.5 mL) was added 4,6-dichloro-1H-indole-2-carbonyl chloride (0.060 g, 0.24 mmol) and diisopropylethylamine (0.031 g, 0.24 mmol). The resulting suspension was stirred at RT for 45 min. The reaction mixture was diluted with dichloromethane and water. A solid precipitated which was filtered and dried under vacuum to give the title compound (0.069 g, 82%) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.12 (br. s., 1H), 9.20 (br. s., 1H), 7.77-7.78 (m, 1H), 7.41-7.52 (m, 3H), 7.33-7.41 (m, 2H), 7.23-7.32 (m, 1H), 7.19-7.20 (m, 1H), 4.54 (s, 2H). ES-LCMS: m/z 522 (M−H).

Workup

  1. customA solid precipitated which
  2. filtrationwas filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-f224d5f9c6d8439c88dfb3ee7aa25174
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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