2-Fluorobenzoyl chloride → tert-Butyl (2-(7-(2-fluoro-4-(2-fluorobenzamido)phenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5-yl)methyl(2-methoxyethyl)carbamate

HRID 409984Notes

Reaction equation

HRID 409984 reaction equation
[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:12][C:13]1[N:17]([CH3:18])[C:16]([C:19]2[S:27][C:26]3[C:21](=[N:22][CH:23]=[CH:24][C:25]=3[O:28][C:29]3[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:30]=3[F:36])[CH:20]=2)=[N:15][CH:14]=1)[CH2:8][CH2:9][O:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[F:47][C:48]1[CH:56]=[CH:55][CH:54]=[CH:53][C:49]=1[C:50](Cl)=[O:51]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:37])[N:7]([CH2:12][C:13]1[N:17]([CH3:18])[C:16]([C:19]2[S:27][C:26]3[C:21](=[N:22][CH:23]=[CH:24][C:25]=3[O:28][C:29]3[CH:34]=[CH:33][C:32]([NH:35][C:50](=[O:51])[C:49]4[CH:53]=[CH:54][CH:55]=[CH:56][C:48]=4[F:47])=[CH:31][C:30]=3[F:36])[CH:20]=2)=[N:15][CH:14]=1)[CH2:8][CH2:9][O:10][CH3:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 57919490tert-Butyl (2-(7-(4-amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5-yl)methyl(2-methoxyethyl)carbamate

Product 1

HCID 58236607tert-Butyl (2-(7-(2-fluoro-4-(2-fluorobenzamido)phenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazol-5-yl)methyl(2-methoxyethyl)carbamateYield 108.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of aniline 46 (300 mg, 0.569 mmol) in DCM (10 mL) at 0° C. was added DIPEA (0.199 mL, 1.137 mmol) and 2-fluorobenzoyl chloride (135 mg, 0.853 mmol) and the suspension was stirred overnight at room temperature. The reaction mixture was concentrated and the residue was partitioned between EtOAc and water. The organic layer was collected, dried and concentrated. The residue was purified using Biotage (eluent EtOAc, 25 g Silicycle HR column) to provide the title compound 356 (400 mg, 0.616 mmol, quantitative yield) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between EtOAc and water
  3. customThe organic layer was collected
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified

Sources & evidence

ORD record
ord-09019c1bbb2a436e90cf5d9527bfd250
Source dataset
uspto-grants-2014_06
Patent number
US08759522B2

Reaction notes

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