Water → 4-(6-Amino-5-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)benzoic acid

HRID 509532Notes

Reaction equation

HRID 509532 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:23]2[O:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:26][N:27]=2)[C:5]([N:8](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)=[N:6][CH:7]=1.B([C:37]1[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=1)(O)O.C([O-])([O-])=O.[Na+].[Na+].O>CC#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:8][C:5]1[N:6]=[CH:7][C:2]([C:37]2[CH:45]=[CH:44][C:40]([C:41]([OH:43])=[O:42])=[CH:39][CH:38]=2)=[CH:3][C:4]=1[C:23]1[O:24][C:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[N:26][N:27]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 67481749tert-Butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate

Product 1

HCID 674816654-(6-Amino-5-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridin-3-yl)benzoic acidYield 55%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of tert-butyl N-[5-bromo-3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2-pyridyl]-N-tert-butoxycarbonyl-carbamate (198.7 mg, 0.3841 mmol), 4-boronobenzoic acid (63.74 mg, 0.3841 mmol) and Na2CO3 (81.42 mg, 0.7682 mmol) was suspended in MeCN (3.213 mL)/water (3.213 mL) and degassed (nitrogen/vacuum cycles). The reaction was then treated with tetrakis(triphenylphosphine)palladium(0) (44.39 mg, 0.03841 mmol), degassed again and heated at 110° C. in the microwave for 30 minutes. The reaction was treated with water (0.5 mL) and heated in the microwave at 110° C. for a further 30 minutes. The reaction mixture was washed with DCM, the aqueous phase acidified to pH1 (by addition of 1M HCl), and resulting precipitate filtered off and washed with water to give the product as an orange solid (75 mg, 55% Yield). MS (ES+) 359.14.

Workup

  1. customdegassed (nitrogen/vacuum cycles)
  2. customdegassed again
  3. additionThe reaction was treated with water (0.5 mL)
  4. temperatureheated in the microwave at 110° C. for a further 30 minutes
  5. washThe reaction mixture was washed with DCM
  6. additionthe aqueous phase acidified to pH1 (by addition of 1M HCl)
  7. customresulting precipitate
  8. filtrationfiltered off
  9. washwashed with water

Sources & evidence

ORD record
ord-4ba81d200c59410bb6508d02fe0a46d5
Source dataset
uspto-grants-2015_08
Patent number
US09096584B2

Reaction notes

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