Diethyl Ether → HCID 49853707, compound

HRID 1503139Notes

Reaction equation

HRID 1503139 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8](C(OC(C)(C)C)=O)[CH:7]=[C:6]2/[C:19](/[C:27]#[CH:28])=[CH:20]/[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+].C[O-].[Na+].C(OCC)C>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2/[C:19](/[C:27]#[CH:28])=[CH:20]/[C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 10942334Sodium MethoxideHCID 86685641HCID 86685641, compound

Product 1

HCID 49853707HCID 49853707, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of (E)-tert-butyl 5-methoxy-3-(1-(pyridin-3-yl)but-1-en-3-yn-2-yl)-1H-indole-1-carboxylate (270 mg, 0.72 mmol, 1.0 eq.) in ethanol (40 mL) were added K2CO3 (1.2 g, 8.6 mmol, 12.0 eq.) and sodium methanolate (232 mg, 4.3 mmol, 6.0 eq.), and then, the reaction was stirred at room temperature for 3 days. The solvent was removed and the residue taken up in ethyl acetate. The organic layer washed with water, dried over MgSO4, filtered through a silica gel pad and then, evaporated under reduced pressure to afford, after trituration with diethyl ether, the compound (58) as a yellowish powder (180 mg, 91%). mp: 136° C.; IR νmax (cm−1): 2089 (νCC alcyne); 1H RMN (DMSO, 300 MHz) δ (ppm): 3.81 (3H, s, 5-methoxy), 4.64 (1H, s, H4′), 6.84 (1H, dd, J6-7=8.9 Hz, J6-4=2.3 Hz, H6), 7.29 (1H, s, H1′), 7.35 (1H, d, J7-6=8.9 Hz, H7), 7.42 (1H, dd, J5″-4″=7.3 Hz, J5″-6″=4.5 Hz, H5″), 7.49 (1H, d, J4-6=2.3 Hz, H4), 7.67 (1H, s, H2), 8.46 (2H, m, H4″ and H6″), 9.03 (1H, s, H2″), 11.37 (1H, s, indolic H); 13C NMR (DMSO, 75.5 MHz) δ (ppm): 55.4 (5-methoxy), 82.5 (C3′), 86.7 (C4′), 102.2 (C4), 111.7 (C6), 112.8 (C7), 114.2 (C2′), 117.7 (C3), 123.2 (C5″), 124.4 (C3a), 126.4 (C1′), 127.0 (C2), 132.2 (C7a), 132.7 (C3″), 134.3 (C4″), 147.9 (C6″), 149.8 (C2″), 154.0 (C5); ESI-MS: m/z 275.1 ([M+H]+); HRESI-MS: m/z 275.1176 (calcd for C18H15N2O+, 275.1184).

Workup

  1. customThe solvent was removed
  2. washThe organic layer washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered through a silica gel pad
  5. customevaporated under reduced pressure
  6. customto afford

Sources & evidence

ORD record
ord-eed29ca110fd4ac89fbbfba5987c1958
Source dataset
uspto-grants-2015_12
Patent number
US09212138B2

Reaction notes

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