1-Pentanethiol → HCID 57548072, 화합물

HRID 660190

반응식

HRID 660190 반응식
Br[C:2]1[N:6]=[CH:5][N:4]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[CH2:21]([SH:26])[CH2:22][CH2:23][CH2:24][CH3:25].C([O-])([O-])=O.[K+].[K+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C(C)=CC=CC=1>[CH2:21]([S:26][C:2]1[N:6]=[CH:5][N:4]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[C:3]=1[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH2:22][CH2:23][CH2:24][CH3:25]

참가 물질

8

반응물 4

HCID 80671-PentanethiolHCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 575480803-[5-bromo-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-pyridine

생성물 1

HCID 57548072HCID 57548072, 화합물수율 30%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 7237O-Xylene용매HCID 8857Ethyl Acetate용매

실험 절차

To a degassed solution of xylene (100 ml) containing 73 (1.82 g, 5.16 mmol), were added 1.25 eq (0.80 ml) of pentane-1-thiol and 1.25 eq of K2CO3 (0.8 g). The resulting mixture was stirred for another 2 hours under N2. Successively were added 10 mol % of Pd2(dba)3 (470 mg) and 20 mol % mmol Xantphos (600 mg). After the addition, the resulting solution was stirred for 18 hours at 130° C. under N2. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with a saturated NaHCO3 solution, dried (Na2SO4), filtered and concentrated. The resulting residue was purified by flash chromatography (diethyl ether followed by ethyl acetate) to afford 3-[5-pentylsulfanyl-3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazol-4-yl]-pyridine (74A) as an oil (530 mg, 30%) and starting material (73, 380 mg, 21%), 1H-NMR (400 MHz, CDCl3): δ 9.38 (d, J=2 Hz, 1H), 8.53 (dd, J=5 Hz, 2 Hz, 1H), 8.42 (dt, J=8 Hz, 2 Hz, 1H), 7.82 (s, 1H), 7.35-7.30 (m, 1H), 5.43 (s, 2H), 3.59-3.54 (m, 2H), 2.66 (t, J=7 Hz, 2H), 1.47-1.38 (m, 2H), 1.28-1.10 (m, 4H), 0.96-0.89 (m, 2H), 0.80 (t, J=7 Hz, 3H), 0.0 (s, 9H).

후처리

  1. additionAfter the addition
  2. stirringthe resulting solution was stirred for 18 hours at 130° C. under N2
  3. washwashed with a saturated NaHCO3 solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (diethyl ether followed by ethyl acetate)

출처 및 근거

ORD 기록
ord-ad11e472c0a5482b892bd9d8b4c40c29
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084473B2

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