2-Methyl-3-butyn-2-ol → HCID 68181823, compound

HRID 1398717Notes

Reaction equation

HRID 1398717 reaction equation
[Br:1][C:2]1[C:3]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15](Br)[CH:16]=3)[CH:11]=[N:10]2)=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH3:19][C:20]([OH:24])([C:22]#[CH:23])[CH3:21]>>[NH2:8][C:5]1[N:4]=[C:3]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:23]#[C:22][C:20]([CH3:21])([OH:24])[CH3:19])[CH:16]=3)[CH:11]=[N:10]2)[C:2]([Br:1])=[CH:7][N:6]=1

Participants

3

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 68181689HCID 68181689, compound

Product 1

HCID 68181823HCID 68181823, compound

Procedure

5-bromo-4-(6-bromoindazol-1-yl)pyrimidin-2-amine (3 g) was reacted with 2-methyl-3-butyn-2-ol (1 eq) via General Procedure Sonagashira Coupling (See, Chinchilla, R.; Najera, C. (2007), “The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry”, Chem. Rev. 107: 874-922) to afford 0.7 g of 4-[1-(2-amino-5-bromo-pyrimidin-4-yl)indazol-6-yl]-2-methyl-but-3-yn-2-ol following flash column chromatography. 4-[1-(2-amino-5-bromo-pyrimidin-4-yl)indazol-6-yl]-2-methyl-but-3-yn-2-ol (0.1 g) was reacted with 1-methyl-4-pyrazoleboronic acid pinacol ester via General Procedure Suzuki Coupling to afford 12.2 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) 374. 1H NMR (400 MHz, DMSO-d6) δ 8.57 (s, 1H), 8.30 (s, 1H), 7.88-7.81 (m, 2H), 7.48 (s, 1H), 7.24 (dd, J=8.3, 1.1 Hz, 1H), 7.05 (s, 2H), 6.98 (s, 1H), 5.47 (s, 1H), 3.73 (s, 3H), 1.48 (s, 6H).

Workup

  1. custom(2007), “The Sonogashira Reaction

Sources & evidence

ORD record
ord-4047efc478314cc98d89edf47468728b
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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