Boron tribromide → HCID 54575927, compound

HRID 579423Notes

Reaction equation

HRID 579423 reaction equation
C[O:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][N:8]([C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[O:14])[CH2:7][CH2:6][C:5]=2[C:4]=1[CH:21]=[O:22].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:12]=[CH:11][C:10]2[CH2:9][N:8]([C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[O:14])[CH2:7][CH2:6][C:5]=2[C:4]=1[CH:21]=[O:22]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 86683390HCID 86683390, compound

Product 1

HCID 54575927HCID 54575927, compoundYield 61.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-methoxy-2-(pyridine-3-carbonyl)-1,2,3,4-tetrahydro-isoquinoline-5-carbaldehyde (62 mg, 0.21 mmol) in dichloromethane (5 mL) stirred under argon at −78° C. was added boron tribromide (0.12 mL, 0.31 g, 1.25 mmol). The reaction was stirred for 1 h, allowed to warm to room temperature and stirred for 2 h. The reaction was quenched by addition of methanol (2 mL) at −78° C. and the mixture was stirred for 1 h. After warming to room temperature, ethyl acetate (3 mL) and diethyl ether (30 mL) were added, upon scratching the product started to precipitate. The mixture was allowed to stand refrigerated overnight, the product was collected, washed with ethyl acetate and dried over P2O5 to give the title compound (48 mg, 0.13 mmol, 61.9%) as a beige powder.

Workup

  1. stirringstirred for 2 h
  2. customThe reaction was quenched by addition of methanol (2 mL) at −78° C.
  3. stirringthe mixture was stirred for 1 h
  4. temperatureAfter warming to room temperature
  5. additionethyl acetate (3 mL) and diethyl ether (30 mL) were added
  6. customto precipitate
  7. waitto stand refrigerated overnight
  8. customthe product was collected
  9. washwashed with ethyl acetate
  10. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-c54f53d50ce84b74b38c6337e33a6aef
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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