2-(Bromomethyl)-3-chloro-1,4-difluorobenzene → HCID 11176598, compound

HRID 602373Notes

Reaction equation

HRID 602373 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13](CC3C=C(F)C=CC=3Br)[C:12](=[O:23])[N:11]([CH3:24])[C:10](=[O:25])[CH:9]=2)[CH2:3]1.[Cl:26][C:27]1[C:34]([F:35])=[CH:33][CH:32]=[C:31]([F:36])[C:28]=1[CH2:29]Br>>[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[N:13]([CH2:29][C:28]3[C:31]([F:36])=[CH:32][CH:33]=[C:34]([F:35])[C:27]=3[Cl:26])[C:12](=[O:23])[N:11]([CH3:24])[C:10](=[O:25])[CH:9]=2)[CH2:3]1

Participants

3

Reactant 2

HCID 27735492-(Bromomethyl)-3-chloro-1,4-difluorobenzeneHCID 11464036Trelagliptin Impurity 47

Product 1

HCID 11176598HCID 11176598, compound

Procedure

The title compound was prepared from compound 1 using the same procedures as in the preparation of compound 10, except that 2-chloro-3,6-di-fluoro-benzyl bromide was used in the place of 2-bromo-5-fluoro-benzyl bromide. 1H NMR (400 MHz, CDCl3-CD3OD 10:1) δ ppm 6.98-7.06 (m, 2H), 6.90 (m, 2H), 5.31 (s, 1H), 5.01-5.20 (ABq, J=24.2, 14.4 Hz, 2H), 3.28-3.37 (m, 2H) 3.13 (s, 3H), 3.01-2.94 (m, 1H), 2.6-2.9 (m, 2H), 2.10 (m, 1H), 1.92 (m, 2H), 1.73 (s, 1H), 1.6-1.75 (m, 2H). MS (ES) [m+H] calc'd for C17H20ClF2N4O2, 385.1; found 385.1.

Sources & evidence

ORD record
ord-7b40db6ecd314970bab05b8c2fe0a54e
Source dataset
uspto-grants-2011_03
Patent number
US07906523B2

Reaction notes

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