4-Carboxyphenylboronic Acid → 4-(7-Methoxyisoquinolin-3-yl)benzoic acid

HRID 2201475Notes

Reaction equation

HRID 2201475 reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.B([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)(O)O>O>[CH3:13][O:12][C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2]([C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[N:3]=[CH:4]2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 3121834-Carboxyphenylboronic AcidHCID 534255653-Chloro-7-methoxyisoquinoline2×

Product 1

HCID 679743114-(7-Methoxyisoquinolin-3-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Followed the procedure described in Compound IV-8 step 1, starting with 3-chloro-7-methoxyisoquinoline (Intermediate 12) and 4-boronobenzoic acid with an alternative isolation procedure: After reaction was complete, the reaction mixture was diluted with H2O (10 mL). The aqueous layer was extracted with EtOAc/MeOH (v/v=10:1, 30 mL×2). Then the aqueous layer was acidified with 2M HCl to pH=6. The precipitate was collected by filtration and washed with MeOH (10 mL), dried under high vacuum to give the product.

Workup

  1. customAfter reaction
  2. extractionThe aqueous layer was extracted with EtOAc/MeOH (v/v=10:1, 30 mL×2)
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with MeOH (10 mL)
  5. customdried under high vacuum
  6. customto give the product

Sources & evidence

ORD record
ord-5544c17078f84c469a71c7578a0ad83d
Source dataset
uspto-grants-2016_06
Patent number
US09364481B2

Reaction notes

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