Acetyl chloride → 1-Acetyl-6-bromo-1,2-dihydrospiro[indole-3,3'-thietane]

HRID 1618785Notes

Reaction equation

HRID 1618785 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:13][S:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:21]([N:8]1[C:6]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:7]=2)[C:10]2([CH2:13][S:12][CH2:11]2)[CH2:9]1)(=[O:23])[CH3:22]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 670953786-Bromospiro[indoline-3,3'-thietane]

Product 1

HCID 582217341-Acetyl-6-bromo-1,2-dihydrospiro[indole-3,3'-thietane]

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of 6-bromo-1,2-dihydrospiro[indole-3,3′-thietane] (0.25 g, 0.96 mmol), 4-dimethylaminopyridine (5.89 mg, 0.048 mmol), and triethylamine (0.269 mL, 1.928 mmol) in DCM (9.64 mL) was added acetyl chloride (0.137 mL, 1.928 mmol). The solution was stirred for 5 min at this temperature, the ice bath was removed and the solution was stirred at rt for 3 h. The reaction was poured into 2N HCl aqueous solution and extracted with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to give 1-acetyl-6-bromo-1,2-dihydrospiro[indole-3,3′-thietane] as a yellow solid. Mass Spectrum (ESI) m/e=297.9 [(M+1) (79Br)] and 300.0 [(M+1) (81Br)].

Workup

  1. customthe ice bath was removed
  2. stirringthe solution was stirred at rt for 3 h
  3. additionThe reaction was poured into 2N HCl aqueous solution
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-40d0ca85abcd4dffb1c1973d48e6be44
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

Loading…