Hydrochloric Acid → HCID 58221582, compound

HRID 1618754Notes

Reaction equation

HRID 1618754 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:15][CH2:14][S:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.CCN(CC)CC.[C:23](Cl)(=[O:25])[CH3:24].Cl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:23]([N:8]1[C:6]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:7]=2)[C:10]2([CH2:15][CH2:14][S:13][CH2:12][CH2:11]2)[CH2:9]1)(=[O:25])[CH3:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 67095488HCID 67095488, compound

Product 1

HCID 58221582HCID 58221582, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred ice-cooled solution of 6-bromo-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran] (0.7 g, 2.46 mmol), 4-dimethylaminopyridine (0.03 g, 0.25 mmol) and Et3N (0.37 g, 3.69 mmol) in DCM (25 mL) was added acetyl chloride (0.21 mL, 2.96 mmol) via syringe. The resulting mixture was stirred at 0° C. for 5 min and at rt for 1.5 h. After this time the mixture was poured into ice and 2N aqueous HCl and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, saturated aqueous NaHCO3, brine, and dried over anhydrous Na2SO4. Purification by column chromatography (EtOAc:hexanes) gave 1-acetyl-6-bromo-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran] as an off-white solid. Mass Spectrum (ESI) m/e=326.0 [(M+1) (79Br)] and 328.0 [(M+1) (81Br)].

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe combined organic extracts were washed with brine, saturated aqueous NaHCO3, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. customPurification by column chromatography (EtOAc:hexanes)

Sources & evidence

ORD record
ord-f67620b711ca4293a8d1010e84bbcae1
Source dataset
uspto-grants-2014_07
Patent number
US08765940B2

Reaction notes

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