Methanesulfonic Acid → HCID 86651950, compound

HRID 1615251Notes

Reaction equation

HRID 1615251 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[NH:4][N:3]=1.C1COCC1.CS(O)(=O)=O.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>C(Cl)Cl>[I:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[N:4]([CH:24]2[CH2:25][CH2:26][CH2:27][CH2:28][O:23]2)[N:3]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 8028TetrahydrofuranHCID 80803,4-dihydro-2H-pyranHCID 178519327HCID 178519327, compound

Product 1

HCID 86651950HCID 86651950, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

An oven-dried round bottom flask under Ar was charged with 3-iodo-1H-indazole-6-carbaldehyde (50 mg, 0.184 mmol), THF (1.5 mL) and CH2Cl2 (1.0 mL). Methanesulfonic acid (1.4 uL, 0.0221 mmol) was added and the solution cooled with an ice-water bath. A solution of 3,4-dihydro-2H-pyran (41 uL, 0.460 mmol) in CH2Cl2 (0.5 mL) was then added dropwise over 15 minutes and the reaction stirred overnight. The solvents were removed in vacuo and the residue purified by column chromatography (silica gel, 99:1 to 98:2 CH2Cl2/MeOH) to give the title compound as a white powder (16 mg, 25%). 1H NMR (400 MHz, CDCl3) δ 10.18 (s, 1H), 8.13 (s, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.62 (d, J=8.4 Hz, 1H), 5.84-5.77 (m, 1H), 4.07-4.02 (m, 1H), 3.83-3.75 (m, 1H), 2.62-2.51 (m, 1H), 2.20-2.10 (m, 2H), 1.86-1.70 (m, 3H); MS ESI 378.9 [M+Na]+, calcd for [C13H13IN2O2+Na]+ 378.99.

Workup

  1. temperaturethe solution cooled with an ice-water bath
  2. customThe solvents were removed in vacuo
  3. customthe residue purified by column chromatography (silica gel, 99:1 to 98:2 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-c3f199fed6a048d8a5a4cc136cd5133a
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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