Benzyl Bromide → HCID 57567393, compound

HRID 423925Notes

Reaction equation

HRID 423925 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-6b7f4dd1604e4728836b33ae5473ab4f
Source dataset
uspto-grants-2012_01
Patent number
US08101767B2

Reaction notes

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