Formic Acid → HCID 68323810, compound

HRID 573570Notes

Reaction equation

HRID 573570 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([Br:24])=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=3)[C:3]=12.[OH-].[Na+].C(O)=O>CS(C)=O.O>[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([Br:24])=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Br:23])[CH:18]=3)[C:3]=12

Participants

6

Reactant 3

HCID 284Formic AcidHCID 14798Sodium HydroxideHCID 68324025HCID 68324025, compound

Product 1

HCID 68323810HCID 68323810, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of ethyl 4-amino-2-bromo-3-(3-bromophenyl)-6-methylthieno[2,3-b]pyridine-5-carboxylate (Description 47) (2.566 g, 5.46 mmol) in DMSO (25 mL) was added aqueous NaOH (2M) (13.64 mL, 27.3 mmol). The mixture was then heated at 150° C. for 1 h. After cooling to RT, the solution was diluted with water (40 mL) and acidified (ca. pH 4-5) with formic acid. The aqueous layer was then extracted with ethyl acetate (50 mL×3), and the combined organic layers were dried and concentrated. Water (excess) was then added to the residue, and a white precipitate crashed-out. The solution was filtered and the precipitate was collected and left to dry overnight in the vacuum oven, to give the title compound (1.861 g). LCMS (A) m/z: 443 [M+1]+, Rt 1.10 min (acidic).

Workup

  1. temperatureAfter cooling to RT
  2. extractionThe aqueous layer was then extracted with ethyl acetate (50 mL×3)
  3. customthe combined organic layers were dried
  4. concentrationconcentrated
  5. additionWater (excess) was then added to the residue
  6. filtrationThe solution was filtered
  7. customthe precipitate was collected
  8. waitleft
  9. customto dry overnight in the vacuum oven

Sources & evidence

ORD record
ord-ff738176fb574500947ed46beea38b1e
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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