Carbon tetrabromide → HCID 68282780, compound

HRID 624050Notes

Reaction equation

HRID 624050 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH2:12][CH2:13]O)=[CH:10][NH:11][C:6]2=[CH:5][CH:4]=1.C(Br)(Br)(Br)[Br:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:16][CH2:13][CH2:12][C:9]1[C:7]2=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=[C:6]2[NH:11][CH:10]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68283239HCID 68283239, compound

Product 1

HCID 68282780HCID 68282780, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-3-yl)ethanol (353 mg, 1.84 mmol) in DCM (5.0 mL), CBr4 (700 mg, 2.11 mmol) was added, then the reaction mixture was cooled to 0° C. and PPh3 (554 mg, 2.11 mmol) was added. After stirring at rt for 2 h the solvent was removed under reduced pressure. Purification was performed by FC (EtOAc/hex 1:9 to 3:7) to yield the title compound as a brown oil, which was stored in the freezer. LC-MS conditions B: tR=0.45 min, [M+H]+=255.03.

Workup

  1. customwas removed under reduced pressure
  2. customPurification

Sources & evidence

ORD record
ord-51a8c0799d104d75a3bfc31b4bc078dc
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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