2-(Bromomethyl)-1,1-difluorocyclopropane → HCID 56942217, compound

HRID 1046494Notes

Reaction equation

HRID 1046494 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9]([C:31]3[CH:32]=[N:33][NH:34][CH:35]=3)=[N:10][N:11](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:7]=2[CH:6]=[CH:5][N:4]=1.Br[CH2:37][CH:38]1[CH2:40][C:39]1([F:42])[F:41]>>[F:41][C:39]1([F:42])[CH2:40][CH:38]1[CH2:37][N:34]1[CH:35]=[C:31]([C:9]2[C:8]3[C:3]([O:2][CH3:1])=[N:4][CH:5]=[CH:6][C:7]=3[NH:11][N:10]=2)[CH:32]=[N:33]1

Participants

3

Reactant 2

HCID 27614022-(Bromomethyl)-1,1-difluorocyclopropaneHCID 136352321HCID 136352321, compound

Product 1

HCID 56942217HCID 56942217, compoundYield 55%

Procedure

Prepared according to the general procedure described in Example 86, by reacting 4-methoxy-3-(1H-pyrazol-4-yl)-1-trityl-1H-pyrazolo[4,3-c]pyridine with 1-bromomethyl-2,2-difluorocyclopropane to give the title compound (29.4 mg, 55% over two steps). LC-MS (Method G): m/z=306.0 [M+H]+, 3.49 min. 1H-NMR (400 MHz, DMSO): δ 13.28 (s, 1H), 8.34 (s, 1H), 8.04 (s, 1H), 7.86 (d, J=5.8, 1H), 7.09 (d, J=5.9, 1H), 4.43-4.26 (m, 2H), 4.06 (s, 3H), 2.37-2.23 (m, 1H), 1.79-1.67 (m, 1H), 1.60-1.49 (m, 1H).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0e45390da36d499ca8485556cebe80c1
Source dataset
uspto-grants-2013_10
Patent number
US08569281B2

Reaction notes

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