alpha-Bromo-o-fluorotoluene → HCID 56942350, compound

HRID 594955Notes

Reaction equation

HRID 594955 reaction equation
[C@H:1]12[NH:8][C@H:5]([CH2:6][CH2:7]1)[CH2:4][CH2:3][CH:2]2[NH:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]2[NH:18][N:19]=[C:20]([C:21]3[CH:22]=[C:23]4[C:27](=[CH:28][CH:29]=3)[N:26]([CH3:30])[N:25]=[CH:24]4)[C:14]=2[CH2:13]1)=[O:11].[F:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34]Br.C(N(C(C)C)CC)(C)C>ClCCl>[F:31][C:32]1[CH:39]=[CH:38][CH:37]=[CH:36][C:33]=1[CH2:34][N:8]1[CH:5]2[CH2:6][CH2:7][CH:1]1[CH:2]([NH:9][C:10]([N:12]1[CH2:17][CH2:16][C:15]3[NH:18][N:19]=[C:20]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[N:26]([CH3:30])[N:25]=[CH:24]5)[C:14]=3[CH2:13]1)=[O:11])[CH2:3][CH2:4]2

Participants

5

Reactant 3

HCID 67968alpha-Bromo-o-fluorotolueneHCID 81531DiisopropylethylamineHCID 66807042HCID 66807042, compound

Product 1

HCID 56942350HCID 56942350, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dichloromethane (1.78 mL) was added to N-((1S,5R)-8-azabicyclo[3.2.1]octan-2-yl)-3-(1-methyl-1H-indazol-5-yl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide (72.3 mg, 0.178 mmol) in a flask. 2-Fluorobenzylbromide (0.0214 mL, 0.178 mmol) was added to the reaction. At room temperature, diisopropylethylamine (0.0920 mL, 0.534 mmol) was added dropwise to the reaction. The reaction was allowed to stir at room temperature for 1 hr. The reaction was quenched using water, was extracted three times using dichloromethane. The dichloromethane extractions were combined, dried over sodium sulfate, filtered, and concentrated. The crude was further purified using HPLC. The endo and exo products were separated. LC-MS: 514.3 [M+H]. LC/MS RT=2.17 and 2.238 min.

Workup

  1. customThe reaction was quenched
  2. extractionwas extracted three times
  3. extractionThe dichloromethane extractions
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was further purified
  8. customThe endo and exo products were separated
  9. customLC/MS RT=2.17 and 2.238 min.

Sources & evidence

ORD record
ord-f7d08102a7e743379bef537eb0edab05
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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