5-Chloro-2-fluoroaniline → HCID 59452617, compound

HRID 419319Notes

Reaction equation

HRID 419319 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][N:12]([CH3:48])[CH2:13][CH2:14][O:15][C:16]1[CH:17]=[C:18]([NH:22][C:23]2[N:28]=[C:27]([C:29]3[N:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]4=[N:31][C:30]=3[C:38]3[CH:39]=[C:40]([CH:45]=[CH:46][CH:47]=3)[C:41](OC)=[O:42])[CH:26]=[CH:25][N:24]=2)[CH:19]=[CH:20][CH:21]=1.[Cl:49][C:50]1[CH:51]=[CH:52][C:53]([F:57])=[C:54]([CH:56]=1)[NH2:55]>C1COCC1>[Cl:49][C:50]1[CH:51]=[CH:52][C:53]([F:57])=[C:54]([NH:55][C:41](=[O:42])[C:40]2[CH:45]=[CH:46][CH:47]=[C:38]([C:30]3[N:31]=[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][N:33]4[C:29]=3[C:27]3[CH:26]=[CH:25][N:24]=[C:23]([NH:22][C:18]4[CH:19]=[CH:20][CH:21]=[C:16]([O:15][CH2:14][CH2:13][N:12]([CH3:11])[CH3:48])[CH:17]=4)[N:28]=3)[CH:39]=2)[CH:56]=1

Participants

5

Reactant 3

HCID 750155-Chloro-2-fluoroanilineHCID 2724254Sodium bis(trimethylsilyl)amideHCID 66649614HCID 66649614, compound

Product 1

HCID 59452617HCID 59452617, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.0M solution of NaHMDS in THF (0.59 mL, 0.59 mmol) was added dropwise to a stirring solution of methyl 3-(3-{2-[(3-{[2-(dimethylamino)ethyl]oxy}phenyl)amino]-4-pyrimidinyl}imidazo[1,2-a]pyridin-2-yl)benzoate (0.100 g, 0.20 mmol) and 5-chloro-2-fluoroaniline (0.09 g, 0.59 mmol) in THF (2 mL) at rt. The reaction mixture was stirred for 0.5 h at room temperature then quenched with methanol and concentrated onto silica gel. Flash chromatography afforded the title compound (0.115 g, 94%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 10.31 (s, 1H), 9.75 (s, 1H), 9.52-9.50 (m, 1H), 8.35 (d, J=5.2 Hz, 1H), 8.31 (s, 1H), 8.01 (d, J=7.7 Hz, 1H), 7.83 (d, J=7.7 Hz, 1H), 7.77-7.72 (m, 2H), 7.61-7.57 (m, 1H), 7.51-7.47 (m, 2H), 7.36-7.24 (m, 3H), 7.17-7.06 (m, 2H), 6.60 (d, J=5.3 Hz, 1H), 6.53 (dd, J=8.2, 2.4 Hz, 1H), 3.95 (t, J=5.9 Hz, 2H), 2.55 (t, J=5.7 Hz, 2H), 2.14 (s, 6H). MS (ES+, m/z) 622 (M+1).

Workup

  1. customthen quenched with methanol
  2. concentrationconcentrated onto silica gel

Sources & evidence

ORD record
ord-ddbf86eb717e42f4a66f94f531b47848
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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