3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine → HCID 59619950, compound

HRID 445696Notes

Reaction equation

HRID 445696 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:24])[C:13](=[O:23])[N:14]([C:15]4[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=4[CH3:20])[C:5]=3[C:4]=2[CH:3]=1.[F:25][C:26]1[C:27]([NH2:41])=[N:28][CH:29]=[C:30](B2OC(C)(C)C(C)(C)O2)[CH:31]=1>>[NH2:41][C:27]1[N:28]=[CH:29][C:30]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:24])[C:13](=[O:23])[N:14]([C:15]5[C:16]([CH3:22])=[N:17][N:18]([CH3:21])[C:19]=5[CH3:20])[C:5]=4[C:4]=3[CH:3]=2)=[CH:31][C:26]=1[F:25]

Participants

3

Reactant 2

HCID 592520523-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 59619981HCID 59619981, compound2×

Product 1

HCID 59619950HCID 59619950, compound

Procedure

The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-3-methyl-1-(1,3,5-trimethyl-1H-pyrazol-4-yl)-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate H) and 3-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridin-2-ylamine (stage 142.1.1) to give the title compound as a yellow foam. (HPLC: tR 2.07 min (Method A); M+H=418 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.92 (s, 1H), 8.05-8.01 (m, 1H), 7.91-7.84 (m, 2H), 7.47-7.42 (m, 1H), 7.35-7.32 (m, 1H), 6.49 (s, 2H), 3.83 (s, 3H), 3.58 (s, 3H), 2.07 (s, 3H), 1.90 (s, 3H))

Workup

  1. customThe title compound was synthesized in a similar manner

Sources & evidence

ORD record
ord-cc864b5bb5d0485495528f8aea65f218
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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