HCID 68182108, compound → HCID 68182067, compound

HRID 1506563Notes

Reaction equation

HRID 1506563 reaction equation
C[O:2][C:3]1[CH:24]=[CH:23][C:6]2[C:7]3[CH:8]=[N:9][N:10]([C:14]4[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH3:22])=[CH:16][CH:15]=4)[C:11]=3[CH2:12][CH2:13][C:5]=2[CH:4]=1>ClCCl>[CH2:20]([C:17]1[CH:16]=[CH:15][C:14]([N:10]2[C:11]3[CH2:12][CH2:13][C:5]4[CH:4]=[C:3]([OH:2])[CH:24]=[CH:23][C:6]=4[C:7]=3[CH:8]=[N:9]2)=[CH:19][CH:18]=1)[CH2:21][CH3:22]

Participants

3

Reactant 1

HCID 68182108HCID 68182108, compound

Product 1

HCID 68182067HCID 68182067, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 7-methoxy-3-(4-propylphenyl)-4,5-dihydro-3H-benzo[e]indazole (Preparation 136B, 570 mg, 1.790 mmol) in dichloromethane (8 mL), cooled to 0° C. was added borontribromide (7.16 mL, 7.16 mmol) dropwise. The reaction mixture was allowed to warm to room temperature slowly and was stirred at room temperature overnight. The reaction mixture was slowly quenched with 1 ml of MeOH. The dark colored solid that formed was filtered and dried under high vacuum to yield 370 mg of product. (yield: 62%). LC/MS M+1=305.1.

Workup

  1. additionwas added borontribromide (7.16 mL, 7.16 mmol) dropwise
  2. customThe reaction mixture was slowly quenched with 1 ml of MeOH
  3. customThe dark colored solid that formed
  4. filtrationwas filtered
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-679226003850473c992410ebacdf8d21
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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