Cesium carbonate → [3-Chloro-2-fluoro-5-(4-methyl-piperazin-1-yl)-benzyl]-carbamic acid tert-butyl ester

HRID 1527482Notes

Reaction equation

HRID 1527482 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13](Br)[CH:12]=[C:11]([Cl:16])[C:10]=1[F:17])([CH3:4])([CH3:3])[CH3:2].[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([N:23]2[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]2)[CH:12]=[C:11]([Cl:16])[C:10]=1[F:17])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 68283623Carbamic acid, N-[(5-bromo-3-chloro-2-fluorophenyl)methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 68284192[3-Chloro-2-fluoro-5-(4-methyl-piperazin-1-yl)-benzyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

was prepared according to Scheme C1 (step A) from (5-bromo-3-chloro-2-fluoro-benzyl)-carbamic acid tert-butyl ester (200 mg, 0.59 mmol), 1-methylpiperazine (71 mg, 0.71 mmol), caesium carbonate (269 mg, 0.83 mmol), palladium (II) acetate (6.6 mg, 0.03 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (24 mg, 0.04 mmol). MS (LC-MS): 358.0 [M]+; tR (HPLC conditions c): 3.98 min.

Workup

  1. customwas prepared
  2. custom3.98 min.

Sources & evidence

ORD record
ord-682c29bffba1483a8c734e94c82c5586
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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