Carbon tetrabromide → HCID 54674389, compound

HRID 869827Notes

Reaction equation

HRID 869827 reaction equation
[CH:1]1([C@H:7]([NH:9][C:10](=[O:19])[C:11]2[CH:16]=[CH:15][C:14]([CH2:17]O)=[N:13][CH:12]=2)[CH3:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Br)(Br)(Br)[Br:40]>C(Cl)Cl>[Br:40][CH2:17][C:14]1[CH:15]=[CH:16][C:11]([C:10]([NH:9][C@@H:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH3:8])=[O:19])=[CH:12][N:13]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54674388HCID 54674388, compound

Product 1

HCID 54674389HCID 54674389, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (R)-N-(1-cyclohexylethyl)-6-(hydroxymethyl)nicotinamide (3.2a, 262 mg, 1 mmol) and Ph3P (472 mg, 1.8 mmol) in CH2Cl2 (10 mL) was cooled to 0° C. and a solution of CBr4 (463 mg, 1.4 mmol) in CH2Cl2 (2 mL) was added dropwise. The reaction was allowed to warm to rt and was stirred overnight. The reaction was concentrated under reduced pressure and the residue purified by column chromatography (silica gel) using 0-40% EtOAc/hexanes to afford 3.3a (156 mg): 1H-NMR (400 MHz, CDCl3) δ 8.91 (s, 1H), 8.11 (dd, J1=8.0 Hz, J2=2.0 Hz, 1H), 7.53 (d, J=8.0 Hz, 1H), 5.98 (d, J=8.0 Hz, 1H), 4.59 (s, 2H), 4.15-4.07 (m, 1H), 1.84-1.68 (m, 5H), 1.49-1.43 (m, 1H), 1.29-1.03 (m, 8H); LC-MS (220 nm), >98%, 325.2 and 327.2 [M+H].

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-1768e103779c4ba5bd7bb00e2aa068e9
Source dataset
uspto-grants-2015_03
Patent number
US08969389B2

Reaction notes

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