Benzyl Bromide → HCID 57567393, compound

HRID 2404822Notes

Reaction equation

HRID 2404822 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([NH:12][C:13]([C:15]2[C:24](=[O:25])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[C:8]([CH3:11])([CH3:10])[CH3:9].C([O-])([O-])=O.[Cs+].[Cs+].[CH:32]1[CH:37]=[CH:36][C:35]([CH2:38]Br)=[CH:34][CH:33]=1>CN(C=O)C>[CH2:38]([O:25][C:24]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][C:15]=1[C:13]([NH:12][C:4]1[CH:5]=[CH:6][C:7]([C:8]([CH3:9])([CH3:11])[CH3:10])=[C:2]([OH:1])[CH:3]=1)=[O:14])[C:35]1[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 575673743-Quinolinecarboxamide, N-[4-(1,1-dimethylethyl)-3-hydroxyphenyl]-1,4-dihydro-4-oxo-

Product 1

HCID 57567393HCID 57567393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of N-(3-hydroxy-4-tert-butyl-phenyl)-4-oxo-1H-quinoline-3-carboxamide (428) (6.7 mg, 0.02 mmol) and Cs2CO3 (13 mg, 0.04 mmol) in DMF (0.2 mL) was added BnBr (10 uL, 0.08 mmol). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was filtered and purified using HPLC to give 4-benzyloxy-N-(3-hydroxy-4-tert-butyl-phenyl)-quinoline-3-carboxamide (275). 1H NMR (400 MHz, DMSO-d6) δ 12.23 (s, 1H), 9.47 (s, 1H), 9.20 (s, 1H), 8.43 (d, J=7.9 Hz, 1H), 7.79 (t, J=2.0 Hz, 2H), 7.56 (m, 1H), 7.38-7.26 (m, 6H), 7.11 (d, J=8.4 Hz, 1H), 6.99 (dd, J=8.4, 2.1 Hz, 1H), 5.85 (s, 2H), 1.35 (s, 9H). HPLC ret. time 3.93 min, 10-99% CH3CN, 5 min run; ESI-MS 427.1 m/z (MH+).

Workup

  1. filtrationThe reaction mixture was filtered
  2. custompurified

Sources & evidence

ORD record
ord-9cc4b0665c1149f2b8c9382f724d3964
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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