2-(3-Butynyloxy)tetrahydro-2H-pyran → HCID 71252922, compound

HRID 1028994Notes

Reaction equation

HRID 1028994 reaction equation
C([Li])CCC.[CH2:6]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:7][C:8]#[CH:9].[C:17]([NH:21][C:22]1[C:31]([CH:32]=[O:33])=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:34]3[C:39]([C:40]([N:42]4[CH2:46][CH2:45][CH2:44][CH2:43]4)=[O:41])=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:47])[CH:28]=2)[N:23]=1)([CH3:20])([CH3:19])[CH3:18]>C1COCC1.[Cl-].[NH4+]>[C:17]([NH:21][C:22]1[C:31]([CH:32]([OH:33])[C:9]#[C:8][CH2:7][CH2:6][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[C:27]([C:34]3[C:35]([CH3:47])=[CH:36][CH:37]=[CH:38][C:39]=3[C:40]([N:42]3[CH2:43][CH2:44][CH2:45][CH2:46]3)=[O:41])[CH:28]=2)[N:23]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

6

Reactant 3

HCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyranHCID 86676841HCID 86676841, compoundHCID 178418339Butyllithium

Product 1

HCID 71252922HCID 71252922, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

n-Butyllithium (2.5 M) (0.624 mL, 1.559 mmol) was added to a solution of 2-(3-butynyloxy)tetrahydro-2H-pyran (0.244 mL, 1.559 mmol) in THF (10 mL) at −78° C. The solution was stirred 1 h at this temperature before warming to 0° C. for 30 min at which time it was slowly added by syringe to a solution of 2-(tert-butylamino)-6-(2-methyl-6-(pyrrolidine-1-carbonyl)phenyl)quinoline-3-carbaldehyde (0.324 g, 0.780 mmol) in THF (10 mL) cooled to −78° C. The resulting dark solution was stirred 10 min at this temperature before warming to 0° C. for 20 min. The reaction mixture was diluted with saturated ammonium chloride and extracted with EtOAc. The combined organic extracts were washed with water, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give (2-(2-(tert-butylamino)-3-(1-hydroxy-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-ynyl)quinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone as an orange oil.

Workup

  1. temperaturecooled to −78° C
  2. stirringThe resulting dark solution was stirred 10 min at this temperature
  3. temperaturebefore warming to 0° C. for 20 min
  4. extractionextracted with EtOAc
  5. washThe combined organic extracts were washed with water, saturated sodium chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-149f44b1ee43417cae2ff27ffb31cb19
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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