Boron tribromide → HCID 57936168, compound

HRID 1435029Notes

Reaction equation

HRID 1435029 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12]3[CH:17]=[CH:16][N:15]=[C:14]([NH:18][CH:19]4[CH2:24][C:23]([CH3:26])([CH3:25])[NH:22][C:21]([CH3:28])([CH3:27])[CH2:20]4)[N:13]=3)=[CH:8][NH:9]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:25][C:23]1([CH3:26])[CH2:24][CH:19]([NH:18][C:14]2[N:13]=[C:12]([C:7]3[C:6]4[C:10](=[CH:11][C:3]([OH:2])=[CH:4][CH:5]=4)[NH:9][CH:8]=3)[CH:17]=[CH:16][N:15]=2)[CH2:20][C:21]([CH3:28])([CH3:27])[NH:22]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 57936207HCID 57936207, compound

Product 1

HCID 57936168HCID 57936168, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

[4-(6-Methoxy-1H-indol-3-yl)-pyrimidin-2-yl]-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (150 mg, 0.4 mmol) was suspended in 6 ml of DCM under argon. After cooling to 0° C., boron tribromide (1.64 ml of a 1M solution in DCM, 1.64 mmol) was added slowly. The cooling bath was removed after 30 minutes and stirring was continued for 16 hours. The reaction was quenched by adding 8 ml of MeOH at 0° C. and the product crystallised from this solution in form of its hydrobromide salt. Yield: 155 mg (94%).

Workup

  1. customThe cooling bath was removed after 30 minutes
  2. customThe reaction was quenched
  3. additionby adding 8 ml of MeOH at 0° C.
  4. customthe product crystallised from this solution in form of its hydrobromide salt

Sources & evidence

ORD record
ord-3ec321cb30c64351ad3daddc67e33dc9
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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