1,2-Dimethoxyethane → HCID 54689926, compound

HRID 1244130Notes

Reaction equation

HRID 1244130 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:12]2[C:20]3[C:19]([OH:21])=[C:18]([C:22]#[N:23])[C:17](=[O:24])[NH:16][C:15]=3[S:14][CH:13]=2)[S:5][C:6]=1[C:7]#[C:8][CH2:9][O:10][CH3:11].CO[CH2:27][CH2:28]OC.C([Sn](CCCC)(CCCC)CCCC)=C>CN(C=O)C>[OH:21][C:19]1[C:20]2[C:12]([C:4]3[S:5][C:6]([C:7]#[C:8][CH2:9][O:10][CH3:11])=[C:2]([CH:27]=[CH2:28])[CH:3]=3)=[CH:13][S:14][C:15]=2[NH:16][C:17](=[O:24])[C:18]=1[C:22]#[N:23]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 81998TributylvinyltinHCID 54689905HCID 54689905, compound

Product 1

HCID 54689926HCID 54689926, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-[4-Bromo-5-(3-methoxy-prop-1-ynyl)-thiophen-2-yl]-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (75 mg, 0.18 mmol, Example 183) was dissolved in 2 mL of 1:1 DMF:DME and at rt, vinyl tributyltin (0.2 mmol) was added. The reaction vessel was flushed with N2, capped and heated to 100° C. for 2 h. The reaction mixture was filtered and filtered again through a plug of silica gel. The residue was taken up in 1:1 MeOH : DMSO, filtered and purified by RP-HPLC to provide the title compound. MS (ESI) m/z 367.0 (M−H+); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.67 (s, 1H), 7.44 (s, 1H), 7.04 (s, 1H), 6.98 (s, 1H), 6.83 (dd, 1H), 5.83 (d, 1H), 5.30 (d, 1H), 4.38 (d, 2H), 4.38 (app d, 2H), 3.43 (app d, 3H).

Workup

  1. customThe reaction vessel was flushed with N2
  2. customcapped
  3. filtrationThe reaction mixture was filtered
  4. filtrationfiltered again through a plug of silica gel
  5. filtrationDMSO, filtered
  6. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-62fa7c67bb4b4dc699dfbadc0f846527
Source dataset
uspto-grants-2006_10
Patent number
US07119205B2

Reaction notes

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