tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate → HCID 68181885, compound

HRID 1398633Notes

Reaction equation

HRID 1398633 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][C:19]([CH3:22])([OH:21])[CH3:20])[CH:15]=3)[CH:10]=[N:9]2)[C:5](Br)=[CH:4][N:3]=1.[C:24]([N:31]1[CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=[N:32]1)(OC(C)(C)C)=O>>[NH2:1][C:2]1[N:7]=[C:6]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]#[C:18][C:19]([CH3:22])([OH:21])[CH3:20])[CH:15]=3)[CH:10]=[N:9]2)[C:5]([C:34]2[CH:33]=[N:32][N:31]([CH3:24])[CH:35]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 68181823HCID 68181823, compound

Product 1

HCID 68181885HCID 68181885, compound

Procedure

4-[1-(2-amino-5-bromo-pyrimidin-4-yl)indazol-6-yl]-2-methyl-but-3-yn-2-ol (0.075 g) was reacted 1-Boc-4-pyrazoleboronic acid pinacol ester via Suzuki Coupling to afford 9.5 mg of 4-[1-[2-amino-5-(1-methylpyrazol-4-yl)pyrimidin-4-yl]indazol-6-yl]-2-methyl-but-3-yn-2-ol following reverse phase hplc purification. MS (Q1) 360. 1H NMR (400 MHz, DMSO) delta 12.71 (s, 1H), 8.62 (s, 1H), 8.30 (s, 1H), 7.84 (d, J=8.3 Hz, 1H), 7.76 (s, 1H), 7.46 (s, 1H), 7.23 (d, J=8.2 Hz, 1H), 7.02 (s, 2H), 5.45 (s, 1H), 1.47 (s, 6H).

Sources & evidence

ORD record
ord-195f3658c36e4f1083170849ed96346f
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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