3-Bromobenzoic acid → HCID 58386659, compound

HRID 74605

Reaction equation

HRID 74605 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH2:16][CH2:15]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([N:17]2[C:18]3[C:14](=[CH:13][C:12]([F:11])=[CH:20][CH:19]=3)[CH2:15][CH2:16]2)=[O:7])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 114563-Bromobenzoic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27744635-Fluoroindoline

Product 1

HCID 58386659HCID 58386659, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.40 g (2.0 mmol) 3-bromobenzoic acid and 0.28 g (2.0 mmol) 5-fluoro-2,3-dihydro-1H-indole in 0.55 mL (4.0 mmol) TEA and 10 mL DCM were combined with 0.64 mg (2.0 mmol) TBTU and stirred overnight at RT. The reaction mixture was extracted with saturated sodium hydrogen carbonate solution and DCM. The combined organic phases were dried on sodium sulphate, filtered and evaporated down. The residue was suspended in MeOH, suction filtered and dried.

Workup

  1. extractionThe reaction mixture was extracted with saturated sodium hydrogen carbonate solution and DCM
  2. customThe combined organic phases were dried on sodium sulphate
  3. filtrationfiltered
  4. customevaporated down
  5. filtrationsuction filtered
  6. customdried

Sources & evidence

ORD record
ord-aeea0957623645d79d3c0b98b15ffdd9
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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