Sodium Carbonate → HCID 10163050, compound

HRID 1358140Notes

Reaction equation

HRID 1358140 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[CH:18]=[C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:20]=[CH:21][C:16]=3[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[O:27][CH3:28])[O:9]2)[CH:5]=[CH:6][CH:7]=1.[C:29]1([CH:35]=[CH:36]B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>CCO.COCCOC.C1(C)C=CC=CC=1.COCCOC.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>[CH3:28][O:27][C:14]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:24])=[O:25])=[CH:18][C:17]=1[CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2](/[CH:36]=[CH:35]/[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:3]=1)[O:9]2

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343812-Phenylvinylboronic acidHCID 10161657HCID 10161657, compound

Product 1

HCID 10163050HCID 10163050, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 131723990HCID 131723990, compoundSolvent

Conditions

Temperature
90 °C

Procedure

A solution of Example 82 (0.046 g, 0.1 mmol) in EtOH/DME/toluene (1 mL, 2:1:1) was added to phenylvinylboronic acid (0.015 g, 0.1 mmol). A solution of Pd(PPh3)4 (0.006 g, 0.005 mmol) in DME (0.5 mL) and aqueous Na2CO3 (20 mg in 0.3 mL H2O, 0.2 mmol) were added. The reaction mixture was heated to 90° C. on a shaker for 15 min then concentrated, diluted with DMSO/MeOH (1:1, 1 mL) and purified by HPLC with 0.1% TFA, water, and CH3CN to provide the titled compound (8 mg, 17%). 1H NMR (500 MHz, CDCL3) δ 8.46 (d, J=8.4 Hz, 1H), 7.50 (m, 4H), 7.36 (dd, J=15.3, 7.8 Hz, 3H), 7.26 (m, 3H), 7.17 (t, J=8.1 Hz, 1H), 7.09 (s, 2H), 6.72 (d, J=9.0 Hz, 1H), 6.65 (m, 2H), 6.24 (s, 1H), 6.01 (s, 1 H), 3.95 (s, 3H), 2.97 (s, 3H); MS (CI, +Q1MS) m/e 483.

Workup

  1. concentrationthen concentrated
  2. additiondiluted with DMSO/MeOH (1:1, 1 mL)
  3. custompurified by HPLC with 0.1% TFA, water, and CH3CN

Sources & evidence

ORD record
ord-c29b445db5b14deba07bb4b9fc6fee1e
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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