1-Azetidinyl(4-bromo-2-fluorophenyl)methanone → HCID 59560327, compound

HRID 1177188Notes

Reaction equation

HRID 1177188 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([N:25]3[CH2:28][CH2:27][CH2:26]3)=[O:24])=[CH:19][CH:18]=2)[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4].N1(C(C2C=CC(Br)=CC=2[F:42])=O)CCC1.COC(C1C=C(O)C=C2OC(C)(C)CC=12)=O>>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([N:25]3[CH2:28][CH2:27][CH2:26]3)=[O:24])=[C:19]([F:42])[CH:18]=2)[CH:8]=[C:7]2[O:11][C:10]([CH3:9])([CH3:12])[CH2:13][C:6]=12)=[O:4]

Participants

4

Reactant 3

HCID 593511201-Azetidinyl(4-bromo-2-fluorophenyl)methanoneHCID 59560026Methyl 6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-carboxylateHCID 595602514-[4-(Azetidine-1-carbonyl)-phenoxy]-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester

Product 1

HCID 59560327HCID 59560327, compound

Procedure

The title compound was prepared in a similar manner as described for Intermediate 35b, from azetidin-1-yl-(4-bromo-2-fluoro-phenyl)-methanone and 6-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester (197e). 1H NMR (400 MHz, CDCl3) δ 7.42 (d, J=7.07 Hz, 1 H) 7.37 (d, J=1.77 Hz, 1 H) 7.29 (dd, J=9.35, 1.52 Hz, 1 H) 7.15 (d, J=2.27 Hz, 1 H) 6.62 (d, J=2.27 Hz, 1 H) 4.16-4.25 (m, 2 H) 4.07-4.16 (m, 2 H) 3.87-3.88 (m, 3 H) 3.33 (s, 2 H) 2.29-2.39 (m, 2 H) 1.51 (s, 6 H); LCMS for C22H22FNO5 m/z 441.30 (M+H)+.

Sources & evidence

ORD record
ord-b870f665b66f4cb988270a5c42b93791
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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