Tributylstannane → HCID 86608939, compound

HRID 2112415Notes

Reaction equation

HRID 2112415 reaction equation
[NH:1]([C:3]1[C:4]2[C:11](I)=[CH:10][N:9]([C@@H:13]3[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@@:14]3([CH3:22])[OH:15])[C:5]=2[N:6]=[CH:7][N:8]=1)[NH2:2].[C]=O.C([SnH](CCCC)CCCC)CCC.C1C[O:41][CH2:40]C1>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>[CH:40]([C:11]1[C:4]2[C:3]([NH:1][NH2:2])=[N:8][CH:7]=[N:6][C:5]=2[N:9]([C@@H:13]2[O:19][C@H:18]([CH2:20][OH:21])[C@@H:16]([OH:17])[C@@:14]2([CH3:22])[OH:15])[CH:10]=1)=[O:41]

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 8028TetrahydrofuranHCID 68879850HCID 68879850, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 86608939HCID 86608939, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The compound from Step 1 is dissolved as a 0.1M solution in THF and 0.2 eq. of tetrakis(triphenylphosphine)palladium (0) are added. While bubbling carbon monoxide gas into the solution, 1 eq. of tributyltin hydride is added over the period of 6 hours. The reaction is then evaporated and subjected to silica gel chromatography, to give the target compound.

Workup

  1. additionare added
  2. additionis added over the period of 6 hours
  3. customThe reaction is then evaporated
  4. customto give the target compound

Sources & evidence

ORD record
ord-8c4527f3a4f44ea39652086c71eb9a25
Source dataset
uspto-grants-2009_04
Patent number
US07524825B2

Reaction notes

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