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

HRID 1527484Notes

Reaction equation

HRID 1527484 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].CO[N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[C:27](=O)([O-])[O-:28].[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:21]2[CH2:22][CH2:23][CH:24]([O:28][CH3:27])[CH2:25][CH2:26]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 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 198313851-MethoxypiperidineHCID 68283623Carbamic acid, N-[(5-bromo-3-chloro-2-fluorophenyl)methyl]-, 1,1-dimethylethyl ester

Product 1

HCID 68284287[3-Chloro-2-fluoro-5-(4-methoxy-piperidin-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 (250 mg, 0.74 mmol), 1-methoxypiperidine (102 mg, 0.89 mmol), caesium carbonate (337 mg, 1.0 mmol), palladium (II) acetate (8.3 mg, 0.04 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (30 mg, 0.05 mmol). MS (LC-MS): 373.0 [M]+; tR (HPLC conditions c): 4.68 min.

Workup

  1. customwas prepared
  2. custom4.68 min.

Sources & evidence

ORD record
ord-95bff7ab03e04479b07d814e2bc96cbc
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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