Hydrochloric Acid → 3-[1-(Benzyloxycarbonyl)indol-3-yl]-1-chloropropan-2-one

HRID 2375570Notes

Reaction equation

HRID 2375570 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][C:21]([OH:23])=O)=[CH:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)[C:25]([Cl:27])=O.[N+](=C)=[N-].Cl>>[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][C:21](=[O:23])[CH2:25][Cl:27])=[CH:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 9550DiazomethaneHCID 65578Oxalyl chlorideHCID 108286661-(Benzyloxycarbonyl)indol-3-yl acetic Acid

Product 1

HCID 161002073-[1-(Benzyloxycarbonyl)indol-3-yl]-1-chloropropan-2-oneYield 87%

Procedure

The procedure described above for the synthesis of 1-chloro-3-[2-(3-methylbenzo[b]thiophen-2-yl)propan-2-one was followed, reacting 1-(benzyloxycarbonyl)indol-3-yl acetic acid (22.49 g, 72.7 mmol) with oxalyl chloride (7.0 mL, 10 g, 80 mmol, then ethereal diazomethane, then dry HCl gas. Flash chromatography over silica gel (15-20% ethyl acetate in hexanes) gave pure product (21.64 g, 87% yield): 1H NMR (400 MHz, CDCl3) δ 3.97 (d, J=1.0 Hz, 2H) 4.15 (s, 2H) 5.45 (s, 2H) 7.27-7.30 (m, 1H) 7.33-7.51 (m, 7H) 7.63 (s, 1H) 8.19 (br. s, 1H); HRMS (ESI+) calcd for C19H17ClNO3 (MH+) 342.0892, found 342.0900.

Sources & evidence

ORD record
ord-df504c2835944208baa0695cbc5b239a
Source dataset
uspto-grants-2008_12
Patent number
US07465798B2

Reaction notes

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