Formic Acid → HCID 21109712, compound

HRID 1766456Notes

Reaction equation

HRID 1766456 reaction equation
[CH2:1]([NH:8][C:9]1[C:17](Br)=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+].C(O)=O>O.O1CCOCC1>[CH2:1]([NH:8][C:9]1[C:17]([C:23]2[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=2)=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 284Formic AcidHCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 21109713HCID 21109713, compound

Product 1

HCID 21109712HCID 21109712, compoundYield 38.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 77 mg (0.25 mmol) 6-benzylamino-5-bromo-nicotinic acid, 58 mg (0.375 mmol) 4-chlorophenyl boronic acid, 9.1 mg 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium (II) dichloromethane complex 1:1 and 0.38 mL 2N Na2CO3 aq. in 0.5 mL water and 2 mL dioxane was heated to 85° C. for 20 h. Formic acid was added, filtered and the mixture was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/HCOOH. The combined product fractions were evaporated to yield 32.4 mg (38%) of the title compound. MS (m/e): 337.3 (M−H).

Workup

  1. filtrationfiltered
  2. customthe mixture was purified by preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile/water/HCOOH
  5. customThe combined product fractions were evaporated

Sources & evidence

ORD record
ord-d4642aafde3a4cf5b39c771d78a1f18c
Source dataset
uspto-grants-2007_06
Patent number
US07229999B2

Reaction notes

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