Benzyl Bromide → HCID 86665675, compound

HRID 81013Notes

Reaction equation

HRID 81013 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[N:15]=[C:14]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:13]=[C:12]([C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)[C:9]=1[C:10]#[N:11].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CS(C)=O.C(OCC)(=O)C>[CH2:28]([O:27][C:24]1[CH:23]=[CH:22][C:21]([C:12]2[C:9]([C:10]#[N:11])=[C:8]([Cl:7])[N:15]=[C:14]([CH:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[CH:13]=2)=[CH:26][CH:25]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 1363723472-Chloro-6-cyclopentyl-4-(4-hydroxyphenyl)nicotinonitrile

Product 1

HCID 86665675HCID 86665675, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (39.3 mg, 0.120 mmol) was added to a solution of 2-chloro-6-cyclopentyl-4-(4-hydroxyphenyl)nicotinonitrile (18 mg, 0.060 mmol) and benzyl bromide (0.014 mL, 0.120 mmol) in DMSO (1 mL). After 16 h at room temperature, the mixture was diluted with ethyl acetate (80 mL), washed with saturated sodium bicarbonate (5 mL), brine (5 mL), dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0-15% ethyl acetate in hexanes, gave 4-(4-(benzyloxy)phenyl)-2-chloro-6-cyclopentylnicotinonitrile as a white solid (20 mg, 85% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.50-7.74 (2H, m), 7.30-7.48 (5H, m), 7.19 (1H, s), 7.00-7.15 (2H, m), 5.13 (2H, s), 3.10-3.34 (1H, m), 2.00-2.32 (2H, m), 1.64-1.95 (6H, m), MS (ES+) m/z: 389 (M+H); LC retention time: 4.431 min (analytical HPLC Method A).

Workup

  1. washwashed with saturated sodium bicarbonate (5 mL), brine (5 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. washSilica gel chromatography, eluting with 0-15% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-caf54cabdb81420281802f0e29738f11
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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