Pyridine → HCID 18439733, compound

HRID 457578Notes

Reaction equation

HRID 457578 reaction equation
N1C=CC=CC=1.[CH2:7]([S:9]([C:12]1[CH:13]=[CH:14][C:15](C)=[C:16]([NH:18][C:19]2[O:20][C:21]([C:24]3[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=3)=[CH:22][N:23]=2)[CH:17]=1)(=[O:11])=[O:10])[CH3:8].[C:32]1(B(O)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.ClCCl.[CH2:44]([O:46]CC)C>CC([O-])=O.CC([O-])=O.[Cu+2]>[CH2:7]([S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:46][CH3:44])=[C:16]([NH:18][C:19]2[O:20][C:21]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH:25]=3)=[CH:22][N:23]=2)[CH:17]=1)(=[O:11])=[O:10])[CH3:8]

Participants

7

Reactant 5

HCID 1049PyridineHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 66827Phenylboronic AcidHCID 18439661HCID 18439661, compound

Product 1

HCID 18439733HCID 18439733, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

Pyridine (5 eq.) was added to a mixture of the title compound of Example 158 (100 mg, 0.27 mmol, 1 eq.), Cu(OAc)2 (1 eq.), phenylboronic acid (2 eq.), powered 4A molecular sieves, and dichloromethane (5 mL). After stirring at RT overnight, the reaction was diluted with diethyl ether and washed with 6N HCl solution. The aqueous layer was separated, made basic with 5N NaOH solution, and extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. Purification by thin layer chromatography gave the title compound (22 mg, 18%) as an off-white solid. 1H NMR (400 MHz, d6-DMSO): δ 9.82 (s, 1H), 8.80 (d, J=2.1, 1H), 7.62 (s, 1H), 7.62 (s, 1H), 7.53–7.42 (m, 5H), 7.30–7.27 (m, 2H), 7.22–7.17 (m, 1H), 7.09 (d, J=8.0, 2H), 6.95 (d, J=7.6, 1H), 3.98 (s, 3H), 3.22 (q, J=7.3, 2H), 1.13 (t, J=7.3, 3H). MS (ES+, m/z)=451 (m+H)+.

Workup

  1. washwashed with 6N HCl solution
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customPurification by thin layer chromatography

Sources & evidence

ORD record
ord-0801a6613dd5496b8d8f792f7eed7484
Source dataset
uspto-grants-2007_03
Patent number
US07189712B2

Reaction notes

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