Tetrahydrofuran → HCID 69289521, compound

HRID 719397Notes

Reaction equation

HRID 719397 reaction equation
C1COCC1.C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34]([O:38][C:39](=[O:48])[NH:40][CH2:41][CH:42]=[CH:43][Si](C)(C)C)([CH3:37])([CH3:36])[CH3:35].I[C:50]1[CH:68]=[CH:67][C:53]([O:54][CH2:55][C:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[N:59]=[C:58]([CH3:66])[CH:57]=2)=[CH:52][CH:51]=1>C1C=CC=CC=1.CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:34]([O:38][C:39](=[O:48])[NH:40][CH2:41][C:42]([C:50]1[CH:68]=[CH:67][C:53]([O:54][CH2:55][C:56]2[C:65]3[C:60](=[CH:61][CH:62]=[CH:63][CH:64]=3)[N:59]=[C:58]([CH3:66])[CH:57]=2)=[CH:52][CH:51]=1)=[CH2:43])([CH3:37])([CH3:36])[CH3:35]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 742671,2-Bis(diphenylphosphino)ethaneHCID 218980594-(4-Iodo-phenoxymethyl)-2-methylquinolineHCID 85157761(3-Trimethylsilanylallyl)-carbamic acid tert-butyl ester

Product 1

HCID 69289521HCID 69289521, compoundYield 14.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
50 °C

Procedure

THF (1.5 mL), Pd(OAc)2 (20 mg, 0.089 mmol, 8% eq) and 1,2-bis(diphenylphosphino)ethane (35.5 mg, 16% eq) were mixed under N2, degassed and stirred to give orange yellow mixture. A premixed solution of (3-trimethylsilanylallyl)-carbamic acid tert-butyl ester (250 mg, 1.09 mmol) from (7b) and 4-(4-iodo-phenoxymethyl)-2-methyl-quinoline (410 mg, 1.0 eq) from (7c) in benzene (3 ml) was added. The resulting mixture was heated at 50° C. over the weekend, then cooled to rt, diluted with ether, washed with water, dried and concentrated. {2-[4-(2-Methyl-quinolin-4-ylmethoxy)-phenyl]-allyl}-carbamic acid tert-butyl ester (65 mg, 14.8%) was obtained after the crude was purified by flash column chromatography (20%–40% ethyl acetate-hexanes). MS Found: (M+H)+=405.

Workup

  1. customdegassed
  2. customto give orange yellow mixture
  3. temperaturecooled to rt
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-991cca04f0504b0c842a52a6be25504a
Source dataset
uspto-grants-2006_11
Patent number
US07132432B2

Reaction notes

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