Hydrochloric Acid → {5-[4-(tert-Butoxycarbonyl)-2-methylphenyl]-2-methoxypyridin-3-yl}boronic acid

HRID 531245Notes

Reaction equation

HRID 531245 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:11][C:10]=2[CH3:22])=[CH:5][C:4]=1[B:23]1[O:27]C(C)(C)C(C)(C)[O:24]1.Cl.I([O-])(=O)(=O)=O.[Na+].C(OCC)(=O)C>O>[C:16]([O:15][C:13]([C:12]1[CH:20]=[CH:21][C:9]([C:6]2[CH:5]=[C:4]([B:23]([OH:27])[OH:24])[C:3]([O:2][CH3:1])=[N:8][CH:7]=2)=[C:10]([CH3:22])[CH:11]=1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 23667635Sodium periodateHCID 89522254Tert-butyl 4-[6-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]-3-methylbenzoate2×

Product 1

HCID 123228619{5-[4-(tert-Butoxycarbonyl)-2-methylphenyl]-2-methoxypyridin-3-yl}boronic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of tert-butyl 4-[6-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]-3-methylbenzoate (INTERMEDIATE 31, 16.0 g, 37.6 mmol), HCl (150 mL, 150 mmol), sodium periodate (24.14 g, 113 mmol) and ethyl acetate (150 mL) was stirred rapidly at room temperature for 1 hour, at which time LCMS showed complete boronate ester hydrolysis. The reaction was diluted with some water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated. The crude was purified by silica gel chromatography to give the title compound. LCMS (M+H)+: 343.95. 1H NMR (500 MHz, CDCl3) δ 8.24 (d, 1H), 8.14 (d, 1H), 7.93 (s, 1H) 7.88 (d, 1H), 7.28 (d, 1H), 5.84 (br, 2H) 4.13 (s, 3H), 2.35 (s, 3H), 1.64 (s, 9H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. customThe crude was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5d51255e55a746b583f19e38b54d5bca
Source dataset
uspto-grants-2016_05
Patent number
US09353101B2

Reaction notes

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