3,5-Dibromo-1-methylpyridin-2(1H)-one → 5-Bromo-3-(5-(methoxymethyl)-1-methyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-one

HRID 593180Notes

Reaction equation

HRID 593180 reaction equation
C[C:2]1(C)[O:7][CH2:6][C:5]2=[CH:8][C:9]([NH:11][C:12]3[C:13](=[O:28])[N:14]([CH3:27])[CH:15]=[C:16](B4OC(C)(C)C(C)(C)O4)[CH:17]=3)=[N:10][N:4]2[CH2:3]1.[Br:30]C1C(=O)N(C)C=C(Br)C=1>>[Br:30][C:16]1[CH:17]=[C:12]([NH:11][C:9]2[CH:8]=[C:5]([CH2:6][O:7][CH3:2])[N:4]([CH3:3])[N:10]=2)[C:13](=[O:28])[N:14]([CH3:27])[CH:15]=1

Participants

3

Reactant 2

HCID 36143503,5-Dibromo-1-methylpyridin-2(1H)-oneHCID 866846053-(6,6-Dimethyl-6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazin-2-ylamino)-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2(1H)-one

Product 1

HCID 580441025-Bromo-3-(5-(methoxymethyl)-1-methyl-1H-pyrazol-3-ylamino)-1-methylpyridin-2(1H)-oneYield 71.3%

Procedure

Following the procedure in Example 335a, and starting with 335b (1.7 g, 12 mmol) and 3,5-dibromo-1-methylpyridin-2(1H)-one (3.2 g, 12 mmol) afforded 336c as a yellow solid (2.8 g, 71%). MS-ESI: [M+H]+ 327. 1H NMR (500 MHz, CDCl3) δ 7.86 (d, J=2.5 Hz, 1H), 7.38 (s, 1H), 6.88 (d, J=2.5 Hz, 1H), 5.86 (s, 1H), 4.41 (s, 2H), 3.82 (s, 3H), 3.58 (s, 3H), 3.36 (s, 3H).

Sources & evidence

ORD record
ord-f755eecf03684a74b7aa1f4fcb77fb44
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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