2-(Tri-n-butylstannyl)oxazole → HCID 90413092, compound

HRID 2175983Notes

Reaction equation

HRID 2175983 reaction equation
[F:1][C:2]1[C:3](I)=[C:4]([C:8]([N:10]2[C@@H:14]3[CH2:15][CH2:16][C@H:11]2[C@H:12]([NH:17][C:18]2[N:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=2)[CH2:13]3)=[O:9])[CH:5]=[CH:6][CH:7]=1.C([Sn](CCCC)(CCCC)[C:34]1[O:35][CH:36]=[CH:37][N:38]=1)CCC>COCCOC.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[C:3]([C:34]2[O:35][CH:36]=[CH:37][N:38]=2)=[C:4]([C:8]([N:10]2[C@@H:14]3[CH2:15][CH2:16][C@H:11]2[C@H:12]([NH:17][C:18]2[N:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=2)[CH2:13]3)=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 154861832-(Tri-n-butylstannyl)oxazoleHCID 90412891HCID 90412891, compound

Product 1

HCID 90413092HCID 90413092, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
145 °C

Procedure

In a microwave vial was dissolved the title compound of Example 277 (30 mg, 0.06 mmol) and 2-(tributylstannyl)oxazole (15 μL, 0.07 mmol) in DME (1 mL). The solution was degassed with N2 for 5 minutes then CuI (1 mg, 0.0045 mmol) and Pd(PPh3)4 (5 mg, 0.0045 mmol) were added. The reaction was purged with N2 and heated at 145° C. for 3 h. The reaction was cooled to rt, filtered through a pad of celite and purified via prep HPLC to give the title compound (19 mg, 72%). MS (ESI) mass calcd. for: C21H17F4N5O2, 447.1; m/z found 448.1 [M+H]+. 1H NMR (500 MHz, Chloroform-d) 8.49 (s, 1H), 8.36 (s, 0.8H), 7.85 (s, 0.8H), 7.76 (s, 0.4H), 7.62-7.45 (m, 1H), 7.43-7.33 (m, 1H), 7.32-7.23 (m, 2H), 7.23-7.09 (m, 1H), 4.91-4.85 (m, 0.4H), 4.78 (d, J=5.4 Hz, 0.6H), 4.42 (td, J=8.6, 2.8 Hz, 0.6H), 4.28 (td, J=8.2, 3.6 Hz, 0.4H), 4.00-3.95 (m, 0.6H), 3.89 (d, J=4.4 Hz, 0.4H), 2.23-1.44 (m, 6H).

Workup

  1. customThe solution was degassed with N2 for 5 minutes
  2. customThe reaction was purged with N2
  3. temperatureThe reaction was cooled to rt
  4. filtrationfiltered through a pad of celite
  5. custompurified via prep HPLC

Sources & evidence

ORD record
ord-5ac7fcc6e8e14cfe95a160b8c7ae12e2
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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