Triethylamine → HCID 86690718, compound

HRID 1473893Notes

Reaction equation

HRID 1473893 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4](P(=O)(OC)OC)[O:3]1.[N:17]1[CH:18]=[CH:19][N:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]=O)[C:21]=12.CCN(CC)CC>C1COCC1>[N:17]1[CH:18]=[CH:19][N:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH:26]=[C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[C:2](=[O:1])[O:3]3)[C:21]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10997174Imidazo(1,2-a)pyridine-8-carbaldehydeHCID 11118213Dimethyl (3-oxo-1,3-dihydro-2-benzofuran-1-yl)phosphonate

Product 1

HCID 86690718HCID 86690718, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonate (610 mg, 2.4 mmol), imidazo[1,2-a]pyridine-8-carbaldehyde (350 mg, 2.4 mmol, 1 equiv.) in THF (5 mL) was added Et3N (0.33 mL 2.4 mmol). The mixture was stirred at rt for 48 h. The precipitation was filtered off and washed with EtOAc. The filtrate was concentrated to give 3-(imidazo[1,2-a]pyridin-8-ylmethylene)isobenzofuran-1(3H)-one (400 mg, 64%) as a yellow solid. Small crude sample (˜20 mg) was purified on RP-HPLC with CH3CN and water as eluent to separated the E/Z isomers (10 mg, 7 mg). 1H NMR (400 MHz, CD3OD) Z-form: δ=8.52 (d, 1H), 7.95-7.91 (m, 2H), 7.62-7.54 (m, 4H), 7.52-7.48 (m, 1H), 7.09 (s, 1H), 7.04 (t, 1H) E-form: δ=8.38 (d, 1H), 8.15 (d, H), 8.05 (d, 1H), 7.95 (d, 1H), 7.90-7.84 (m, 2H), 7.67 (t, 1H), 7.64 (s, 1H), 7.33 (s, 1H), δ 7.05 (t, 1H). LRMS (M+H+) m/z 263.1

Workup

  1. customThe precipitation
  2. filtrationwas filtered off
  3. washwashed with EtOAc
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-fc94cc3da1cf45e68fcbcb19bc6493d1
Source dataset
uspto-grants-2015_04
Patent number
US09018210B2

Reaction notes

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